Haven't been to the Preakness since '88 (geez I'm gettin' old!) but what I remember is that it is nowhere near anyplace you'd want to be either before or afterward. That said, I've spent some time in Baltimore and Mt. Washington is a nice section of town just north and there are some decent eats and pubs there. Not sure about lodging. Probably need to get outside the beltway in Hunt Valley, Timonium, Pikesville, etc.
If you're going the tourist route, as mentioned the Inner Harbor is nice, expensive, but nice. The Aqurimum, Pier 6, Federal Hill, Cross Street Market, and Camden Yards are all within walking distance and it's pretty safe.
To drive from the Inner Harbor to Pimlico will put you through the middle of the set from "The Wire". Scary place. Take the expressway north (I think it's called the JFK or something). DO NOT drive through the inner city.
If you head up towards Timonium, a GREAT rib place is called the Corner Stable. You'll have to google it - I think it is on Cockeysville Rd. Near the Fairgrounds (where they hold the Fasig-Tipton sale). Speaking of which, If you're into it - that sale is usually going on the week before the Preakness and if you've never been to a thoroughbred sale, you owe it to yourself to check it out.
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